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Aryl Annulation: A Powerful Simplifying Retrosynthetic Disconnection. 芳基环化：一种功能强大的简化逆合成断裂法。
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2024-01-01 Epub Date: 2022-11-21 DOI: 10.1055/a-1959-2088
Rachel M Gillard, Jianjun Zhang, Richard Steel, Jocelyn Wang, Jessica L Strull, Bin Cai, Nilanjana Chakraborty, Dale L Boger
{"title":"Aryl Annulation: A Powerful Simplifying Retrosynthetic Disconnection.","authors":"Rachel M Gillard, Jianjun Zhang, Richard Steel, Jocelyn Wang, Jessica L Strull, Bin Cai, Nilanjana Chakraborty, Dale L Boger","doi":"10.1055/a-1959-2088","DOIUrl":"10.1055/a-1959-2088","url":null,"abstract":"<p><p>Retrosynthetic deconstruction of a core aromatic ring is an especially simplifying retrosynthetic step, reducing the complexity of the precursor synthetic target. Moreover, when implemented to provide a penultimate intermediate, it enables late-stage divergent aryl introductions, permitting deep-seated core aryl modifications ordinarily accessible only by independent synthesis. Herein, we highlight the use of a ketone carbonyl group as the functionality to direct such late-stage divergent aryl introductions onto a penultimate intermediate with a projected application in the total synthesis of vinblastine and its presently inaccessible analogs containing indole replacements. Although the studies highlight this presently unconventional strategy with an especially challenging target in mind, the increase in molecular complexity (intricacy) established by the synthetic implementation of the powerful retrosynthetic disconnection, the use of a ketone as the precursor enabling functionality, and with adoption of either conventional or new wave (hetero)aromatic annulations combine to define a general and powerful strategy suited for wide-spread implementation with near limitless scope in target diversification.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10745204/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78186826","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Dealkenylative Functionalizations: Conversion of Alkene C(sp3)-C(sp2) Bonds into C(sp3)-X Bonds via Redox-Based Radical Processes. 脱烯官能化：通过基于氧化还原的自由基过程将烯的 C(sp3)-C(sp2) 键转化为 C(sp3)-X 键。
IF 2.6 4区 化学
Synthesis-Stuttgart Pub Date : 2024-01-01 Epub Date: 2023-04-12 DOI: 10.1055/a-2044-4571
Brady W Dehnert, Jeremy H Dworkin, Ohyun Kwon
{"title":"Dealkenylative Functionalizations: Conversion of Alkene C(sp<sup>3</sup>)-C(sp<sup>2</sup>) Bonds into C(sp<sup>3</sup>)-X Bonds via Redox-Based Radical Processes.","authors":"Brady W Dehnert, Jeremy H Dworkin, Ohyun Kwon","doi":"10.1055/a-2044-4571","DOIUrl":"10.1055/a-2044-4571","url":null,"abstract":"<p><p>This review highlights the history and recent advances in dealkenylative functionalization. Through this deconstructive strategy, radical functionalizations occur under mild, robust conditions. The reactions described proceed with high efficiency, good stereoselectivity, tolerate many functional groups, and are completed within a matter of minutes. By cleaving the C(sp<sup>3</sup>)-C(sp<sup>2</sup>) bond of terpenes and terpenoid-derived precursors, rapid diversification of natural products is possible.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11147281/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73531352","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
SYNFORM ISSUE 2023/12 Synform issue 2023/12
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/s-0040-1720617
Matteo Zanda
{"title":"SYNFORM ISSUE 2023/12","authors":"Matteo Zanda","doi":"10.1055/s-0040-1720617","DOIUrl":"https://doi.org/10.1055/s-0040-1720617","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134992841","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/s-0040-1720098
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720098","DOIUrl":"https://doi.org/10.1055/s-0040-1720098","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134992844","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization 碱基催化环化2-氧-2-(氨基)乙二硫酸酯合成2,4-和2,5-二取代1,3-噻唑的区域选择性
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/a-2210-6357
Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva
{"title":"Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization","authors":"Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva","doi":"10.1055/a-2210-6357","DOIUrl":"https://doi.org/10.1055/a-2210-6357","url":null,"abstract":"We herein report efficient methods for synthesis of 2,4- and 2,5-disubstituted-1,3-thiazoles 3(a-i) and 5(a-k) by the cyclization of 2-oxo-2-(amino)ethanedithioates with TosMIC and α-haloketones in high yields. The structures 3a and 5a were confirmed based on X-ray crystallographic studies. In addition, investigation of ground state geometry, electronic and molecular structural properties, FMOs, global reactivity descriptors, MEP and NCI analyses predicted to access the information related to the stability, reactivity, and strength of the interactions present in the molecules by quantum chemical calculations. Further, the potency of derivatives tested against the SARS-Cov2 receptor (PDB ID: 7mc6) via molecular docking approach with binding scores of –6.0 to –8.4 kcal/mol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134993136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs 5-(三烷基)硅基戊-1-烯-4-炔-3-酮与肼的反应:合成含唑基发光物质的原始途径
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-13 DOI: 10.1055/s-0043-1763601
Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova
{"title":"Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs","authors":"Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova","doi":"10.1055/s-0043-1763601","DOIUrl":"https://doi.org/10.1055/s-0043-1763601","url":null,"abstract":"Abstract On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136282055","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of All Regioisomers of 2-Aryl Azaindole-3-acetic Acid Derivatives 2-芳基氮唑-3-乙酸衍生物所有区域异构体的合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/a-2206-5900
Taewook Kim, Ju Hyeon Park, Cheol Jeong, Eunjoon Park, Jong Mu Kim, You-Jin Kim, Jung-Nyoung Heo, Cheol-Hong Cheon
{"title":"Synthesis of All Regioisomers of 2-Aryl Azaindole-3-acetic Acid Derivatives","authors":"Taewook Kim, Ju Hyeon Park, Cheol Jeong, Eunjoon Park, Jong Mu Kim, You-Jin Kim, Jung-Nyoung Heo, Cheol-Hong Cheon","doi":"10.1055/a-2206-5900","DOIUrl":"https://doi.org/10.1055/a-2206-5900","url":null,"abstract":"A novel protocol was developed for synthesizing 2-aryl substituted azaindole-3-acetic acid derivatives from 2-aminoazacinnamic acid derivatives and aryl aldehydes through an imino-Stetter reaction. Condensation of 2-aminoazacinnamic acid derivatives with aldehydes forms the corresponding aldimines, which are then treated with cyanide to yield the desired 2-aryl substituted azaindole-3-acetic acid derivatives. Notably, this protocol could be employed for the synthesis of all regioisomers of azaindole-3-acetic acid derivatives by using the appropriate azacinnamic acid derivatives.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135392120","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous Catalyzed Dehydrogenative Csp-Csp Homocoupling of Terminal Acetylenes 电氧化还原亚铜催化末端乙炔脱氢Csp-Csp均偶联制备1,3-丁二炔
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/a-2206-6023
Murugan Krishnan, Kathiresan Murugavel, Chandrasekar Praveen
{"title":"Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous Catalyzed Dehydrogenative Csp-Csp Homocoupling of Terminal Acetylenes","authors":"Murugan Krishnan, Kathiresan Murugavel, Chandrasekar Praveen","doi":"10.1055/a-2206-6023","DOIUrl":"https://doi.org/10.1055/a-2206-6023","url":null,"abstract":"Herein, we have disclosed the oxidative homocoupling of terminal alkynes under electrochemically generated cuprous catalysis. The scope of this protocol is established by preparing an array of structurally and electronically different 1,3-butadiyne derivatives. Good synthetic yields, functional group tolerance, oxidant-free conditions and no cross-selectivity are some of the intrinsic advantages of this methodology. The developed chemistry features the electro-redox formation of copper-acetylide, an intermediate appropriate for the Csp-Csp coupling step. The chemical state of copper in the acetylide intermediate was found be Cu(I) as confirmed by click-trapping experiments, CV, EPR and XPS. Competition reaction to determine the reactivity of electronically dissimilar acetylenes revealed that the product ratio is rather dependent on the electronic nature of alkynyl substituents. To highlight the synthetic value of the products, selected diynes were subjected to chemical diversification.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135392121","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A 7A型肺炎链球菌荚膜多糖六糖重复单元的快速合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/s-0040-1720095
Samim Sahaji, Pradip Shit, Anup Kumar Misra, Swapan Kumar Jana
{"title":"Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A","authors":"Samim Sahaji, Pradip Shit, Anup Kumar Misra, Swapan Kumar Jana","doi":"10.1055/s-0040-1720095","DOIUrl":"https://doi.org/10.1055/s-0040-1720095","url":null,"abstract":"Abstract The hexasaccharide repeating unit corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 7A has been synthesized in good yield using [3+2+1] block synthetic strategy. The synthetic strategy involved a number of challenging stereoselective glycosylation steps, which include β-selective glycosylation of l-rhamnosyl thioglycoside donor, α-selective glycosylations of 2-azido-2-deoxy-d-glucopyranosyl thioglycoside donor and d-galactopyranosyl donor together with the formation of β-glycoside of d-galactosamine moiety and α-glycoside of l-rhamnosyl moiety. Suitably functionalized thioglycosides have been used as glycosyl donors and a combination of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf­) has been used as glycosylation promoter.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135340663","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Sequential One-Pot Synthesis of β-Amino-γ-keto-malonates from Nitro-Substituted Donor-Acceptor Cyclopropanes 硝基取代给受体环丙烷一锅法合成β-氨基-γ-酮丙二酸酯
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-08 DOI: 10.1055/a-2206-3750
Selvi Subramani, Meenakshi Maniarasu, Visalini Chidambaram, Kannupal Srinivasan
{"title":"Sequential One-Pot Synthesis of β-Amino-γ-keto-malonates from Nitro-Substituted Donor-Acceptor Cyclopropanes","authors":"Selvi Subramani, Meenakshi Maniarasu, Visalini Chidambaram, Kannupal Srinivasan","doi":"10.1055/a-2206-3750","DOIUrl":"https://doi.org/10.1055/a-2206-3750","url":null,"abstract":"A sequential one-pot procedure has been developed for the access of β-Amino-γ-keto-malonates from nitro-substituted donor-acceptor cyclopropanes and four different N-compounds. The reaction proceeds through in situ generation of aroylmethylidenemalonates from the nitro cyclopropanes via Kornblum type ring-opening oxidation using DMSO and subsequent aza-Michael addition with the N-compounds. To prove the synthetic utility of the resulting products, one of them was transformed into a pyridazinone derivative.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135391418","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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